N-Boc-N-methyl-(S)-2-allylglycine is a Boc-protected amino acid with an allyl substituent that provides synthetic versatility. The N-methyl group introduces conformational restriction and modulates backbone interactions. Researchers use it in designing peptidomimetics and exploring steric influences on folding. Its reactive side chain supports further derivatization.
CAT No: R2165
CAS No:136092-76-7
Synonyms/Alias:N-Boc-N-methyl-(S)-2-allylglycine;136092-76-7;(S)-2-((tert-Butoxycarbonyl)(methyl)amino)pent-4-enoic acid;(2S)-2-[(tert-butoxycarbonyl)(methyl)amino]pent-4-enoic acid;MFCD17214445;SCHEMBL2968987;ZPXOGEHHZSOFJX-QMMMGPOBSA-N;LFA09276;N-Boc-N-methyl-(S)-2-allylglycine ee;CS-0101715;D76221;(S)-2-(tert-butoxycarbonyl(methyl)-amino)pent-4-enoic acid;(2S)-2-{[(tert-butoxy)carbonyl](methyl)amino}pent-4-enoic acid;(2S)-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]pent-4-enoic acid;
N-Boc-N-methyl-(S)-2-allylglycine is a synthetic amino acid derivative characterized by the presence of a tert-butyloxycarbonyl (Boc) protecting group, an N-methyl substitution, and an allyl side chain on the (S)-enantiomer of glycine. As a non-proteinogenic amino acid, it serves as a valuable building block in advanced peptide chemistry and organic synthesis. Its unique structural features enable the introduction of both conformational constraints and reactive functional groups into target molecules, making it particularly relevant for researchers engaged in the design of structurally diverse and functionally specialized peptides. The Boc group provides temporary protection during multi-step synthesis, while the N-methylation and allyl substituent offer opportunities for modulating molecular properties and facilitating selective downstream modifications.
Peptide Synthesis: In peptide research and development, N-Boc-N-methyl-(S)-2-allylglycine is widely utilized as a non-standard amino acid monomer for the assembly of modified peptides. Its N-methylation disrupts conventional hydrogen bonding patterns, enabling the generation of peptides with enhanced proteolytic stability and altered secondary structures. The Boc group serves as a removable protecting group compatible with standard solid-phase peptide synthesis (SPPS) protocols, allowing for efficient incorporation of this residue at specific positions within peptide chains. Researchers often employ this compound to introduce backbone rigidity or to create peptide analogs with improved pharmacokinetic properties for structure-activity relationship (SAR) studies.
Conformational Analysis: The incorporation of N-methyl and allyl functionalities into peptide sequences facilitates the exploration of conformational landscapes in synthetic peptides. By restricting backbone flexibility and introducing steric bulk, this amino acid analog enables detailed investigations into the relationship between peptide structure and biological function. It is particularly valuable for probing the effects of side-chain modifications on peptide folding, stability, and receptor interactions, thereby supporting the rational design of bioactive molecules with tailored properties.
Chemical Ligation Strategies: The allyl group present in N-Boc-N-methyl-(S)-2-allylglycine offers a versatile chemical handle for selective post-synthetic modifications. It can participate in a variety of ligation reactions, such as olefin metathesis or cross-coupling, enabling the site-specific introduction of novel functionalities or reporter groups into peptides and peptidomimetics. This reactivity is especially beneficial for the development of labeled probes, conjugates, or for the immobilization of peptides onto solid supports in chemical biology and material science applications.
Protease Resistance Studies: The presence of an N-methyl group in this amino acid derivative is known to confer resistance to enzymatic cleavage by many proteases. Researchers exploit this property to design peptide sequences that are more stable in biological environments, thereby facilitating the study of degradation pathways and the development of degradation-resistant analogs. Such applications are critical in the evaluation of peptide stability for use in biochemical assays, biomaterials, or as research tools in enzymology.
Combinatorial Library Construction: N-Boc-N-methyl-(S)-2-allylglycine is frequently incorporated into combinatorial peptide libraries to expand the chemical diversity and explore novel sequence motifs. Its inclusion allows for the systematic investigation of non-natural amino acid effects on peptide activity, selectivity, and binding affinities. This approach is instrumental in high-throughput screening programs aimed at identifying new ligands, inhibitors, or molecular scaffolds for biochemical and biotechnological research. The compound's compatibility with automated synthesis platforms further enhances its utility in library design and discovery workflows.
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